Nitrogen → 3-(4-Methoxyimidazo[5,1-f][1,2,4]triazin-7-yl)cyclobutanone

HRID 449016Notes

Reaction equation

HRID 449016 reaction equation
N#N.[CH3:3][O:4][C:5]1[N:6]=[CH:7][N:8]=[N:9][C:10]=1[CH2:11][NH:12][C:13]([CH:15]1[CH2:18][C:17](=[O:19])[CH2:16]1)=O.CC#N.O=P(Cl)(Cl)Cl>CN(C=O)C>[CH3:3][O:4][C:5]1[C:10]2=[CH:11][N:12]=[C:13]([CH:15]3[CH2:18][C:17](=[O:19])[CH2:16]3)[N:9]2[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 66915404N-[(5-methoxy-1,2,4-triazin-6-yl)methyl]-3-oxocyclobutanecarboxamide

Product 1

HCID 669155953-(4-Methoxyimidazo[5,1-f][1,2,4]triazin-7-yl)cyclobutanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an oven-dried flask filled with N2 was added N-[(5-methoxy-1,2,4-triazin-6-yl)methyl]-3-oxocyclobutanecarboxamide (2.40 g, 0.00833 mol) followed by MeCN (200 mL) and DMF (40 mL). The reaction mixture was treated with POCl3 (3.1 mL, 0.033 mol) dropwise at 0° C. under N2 over 10 min. The reaction was stirred at rt overnight. The reaction mixture was concentrated and poured into ice, saturated aqueous NaHCO3 solution was added to adjust the pH to 7. The mixture was extracted with DCM (150×3). The organic extracts were combined, dried (Na2SO4) and concentrated under reduced pressure to give a crude residue, which was then purified by flash chromatography on silica gel using hexanes:EtOAc (1:1) as the eluent.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into ice, saturated aqueous NaHCO3 solution
  3. additionwas added
  4. extractionThe mixture was extracted with DCM (150×3)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2de9036ad8b43e8a7f9777ca4228c63
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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